1,1-Bis(2,2-dimethylpropoxy)-N,N-dimethylmethanamine → HCID 20491754, compound

HRID 434640Notes

Reaction equation

HRID 434640 reaction equation
C(OC(OCC(C)(C)C)N(C)C)C(C)(C)C.[Cl:17][C:18]1[CH:19]=[N:20][C:21](=[O:24])[NH:22][CH:23]=1.O[CH2:26][C:27]1[S:28][CH:29]=[CH:30][C:31]=1[CH3:32]>CN(C)C=O>[Cl:17][C:18]1[CH:19]=[N:20][C:21](=[O:24])[N:22]([CH2:26][C:27]2[S:28][CH:29]=[CH:30][C:31]=2[CH3:32])[CH:23]=1

Participants

5

Reactant 3

HCID 786231,1-Bis(2,2-dimethylpropoxy)-N,N-dimethylmethanamineHCID 1085785-Chloro-2(1H)-pyrimidinoneHCID 12875263(3-Methylthiophen-2-yl)methanol

Product 1

HCID 20491754HCID 20491754, compoundYield 28.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

N,N-Dimethylformamide dineopentyl acetal (2.70 ml) was added to a stirred suspension of 5-chloropyrimidin-2-one (783 mg) and 2-hydroxymethyl-3-methylthiophene (1.077 g) in dry N,N-dimethylformamide (15 ml) under nitrogen. The resulting solution was then heated at 90° C. under nitrogen. After 0.5 h the reaction mixture was evaporated to a dark brown crystalline solid (1.812 g). The solid was subjected to column chromatography on silica (70-230 mesh) (180 g) developing with chloroform-ethanol, 29:1. The resulting light brown crystalline solid (694 mg) was crystallised twice from acetone to give buff needles of the title thiophene (417 mg), m.p. 135°-145° C., λmax 230 nm (ε 16,420), 335 nm (ε 3,830), λinf 250 nm (ε 5,800).

Workup

  1. customAfter 0.5 h the reaction mixture was evaporated to a dark brown crystalline solid (1.812 g)
  2. customThe resulting light brown crystalline solid (694 mg) was crystallised twice from acetone

Sources & evidence

ORD record
ord-7b1a5d07315e4978bab5513b63d2f7ed
Source dataset
uspto-grants-1983_08
Patent number
US04399140

Reaction notes

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